Aluminium lithium hydride → HCID 118307051, compound

HRID 921250Notes

Reaction equation

HRID 921250 reaction equation
[CH2:1]([C:4]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:5]=1[C:6](OC)=[O:7])[CH:2]=[CH2:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([C:4]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:5]=1[CH2:6][OH:7])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118307146HCID 118307146, compound

Product 1

HCID 118307051HCID 118307051, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 2-allyl-4,5-difluorobenzoate (360 mg, 1.697 mmol) in THF (4 mL) was added LAH (3.39 mL, 3.39 mmol) and the reaction was stirred at rt for 1 h. It was then quenched with NH4Cl and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to isolate (2-allyl-4,5-difluorophenyl)methanol (150 mg, 0.814 mmol, 48.0% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.34-7.24 (m, 1H), 7.08-6.97 (m, 1H), 5.96 (ddt, J=16.8, 10.4, 6.2 Hz, 1H), 5.14 (d, J=10.0 Hz, 1H), 5.03 (d, J=17.1 Hz, 1H), 4.67 (d, J=5.1 Hz, 2H), 3.40 (d, J=6.1 Hz, 2H).

Workup

  1. customIt was then quenched with NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto obtain an oil, which
  7. customwas then purified by biotage
  8. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-7a27bf2e37ab4fbf90bd489ba1fbe3f9
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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